Organized crime has existed in Chicago for over a century, and actually originated well before 1919 - the year Prohibition was ratified as the 18th Constitutional Amendment. It appears to be a trend for the criminal to make a business out of any illegal activities that could possibly bring forth profit, and "organized crime always seeks to commercialize and to exploit human nature" (Landesco, 281). Therefore, it is no surprise that gangsters found other lucrative markets to extort before the illegalization of alcohol. Two of the most common markets were prostitution, and gambling.


Gambling is an example of a business that was run and regulated by gangsters with the intent of earning significant profits. Gambling typically appeared in the forms of roulette, craps, various card games including faro, and perhaps most popularly, betting on horse races. The appeal to the gangster of managing gambling operations, which were often disguised as pool halls, is partly due to the illegality of gambling at the time, and also because the demand for such opportunities was present in the city of Chicago. This demand was further amplified by the hardships of the Depression because of the hopes these poor, distraught Chicagoans had of being released from their troubles by beating the odds and winning a big bet.

This desperation of lower class Chicagoans during the Depression, and their turn to gambling in response to financial struggles, are exemplified in Farrell's Studs Loningan. In this time period when "collecting bills … [was] sure one hell of a job" (Farrell, 586) and a father had to resort to asking his son to borrow money, the bookie was flourishing and experiencing the high-life. Phil Rolfe, the character who managed a horse race betting joint, is such an example. Although many, including Studs and his family, were forced out of work by the Depression, Phil states that business was "really a little more than fair" (Farrell, 665). While Mr. Lonigan's painting business was going under, Phil Rolfe was expanding his joint by adding "more space, more blackjack tables, a roulette wheel, a table for poker and craps, and some nice looking furniture … [while expecting] twice as much revenue" (Farrel, 665).

Although Phil Rolfe was not depicted in the novel Studs Lonigan as a gangster, gambling joints such as the one he managed were often organized and overseen by gangsters such as Al Capone, or previously by gambling kings such as Mont Tennes or James O'Leary. The successful operation of gambling joints was limited to such gangsters belonging to powerful groups of organized criminals, for it relied on the influence these groups had on the government and police forces in Chicago. "Since gambling [was] illegal, it [could not] exist except by defeating the law, which [was] accomplished partly by influencing elections through contributions to campaign funds or by the bribery of officials" (Landesco, 45). The immense profits that gangsters received from bootlegging alcohol during Prohibition allowed them to offer more significant bribes to a wider range of government agents, which allowed their gambling circuits to become even more expansive, thus leading to a revolution of this aspect of organized crime (Organized Crime After Prohibition). This association of personnel of gambling facilities was seen in Algren's The Man with the Golden Arm, where Frankie and the police were both involved with Schwiefka's business. This novel also illustrates the influence hustlers (a general category that includes gangsters) had over the police when Frankie is imprisoned. After the manager of the gambling joint Frankie deals at speaks with city officials at the jail, he states to Frankie, "What I said is you're gettin' out in half a hour 'n the super hisself couldn't put the fix in faster" (Algren 1976, 24).

The former residence of Mont Tennes at 632 West Belden Avenue in Lincoln Park. Tennes clearly was quite a wealthy man from his gambling profits (Citation).

Although horse racetracks were eventually banned in Chicago in 1904 by Mayor Carter Harrison II, betting on races still took place. This was possible through John Payne's invention of a telegraph-wire system to relay the results of horse races across the country to specific gambling hideouts in Chicago. The inventor, a previous employee of the Western Union Telegraph Company, sold this service to Mont Tennes, who charged the managers of betting joints for access to this information he controlled. Tennes thus monopolized access to these horse race results and betting on horse races altogether, which upset his competition. Because of the profits involved in the gambling business, conflicts between Tennes' gang and other gangs such as that of O'Leary led to war between the gangs. However, for many years, Tennes was the victor, and for this, he became a very rich mobster. Mont Tennes was forced into retirement in the 1920's by Al Capone and his gang. Capone, along with his massive earnings from bootlegging, was able to buy off even the mayor of the city and propagate his gambling business in the city and into the suburbs of Chicago (Click here to read more about organized crime in Chicago after Prohibition).


Another example of an illegal activity in which the gangster was heavily involved was prostitution. In the city of Chicago, gangsters created, operated, and managed hundreds of whorehouses, which often had the false front of being a roadhouse, saloon, or resort. As suggested by Farrell's Studs Loningan, these were a common part of life for many a Chicagoan, especially younger adolescents such as Studs Lonigan, who along with his gang of friends, were frequent customers. One of the whorehouses these boys visit is named the "Cannonball Inn", which is a cover for what actually occurs in the building (Farrell, 300).

Above is a picture of a whorehouse at 310 North Peoria Street in Chicago during the early 1900's (Citation).

This aspect of organized crime (prostitution) was also heavily dependent on affiliations and alliances between the gangster, politician, and police officer. Business, and the amount of profit received through prostitution operations, fluctuated as different mayors came and passed, for some could be bought out, and others could not. Mayor William Hale Thompson was an example of the prior case, and during his terms, gangster activities such as prostitution thrived. A December issue of the Daily News in 1922 stated, "the lawless days of the famous 'red-light' district when the demimonde and professional gambler, under the appraising eye of the police, were once more restored … where … Thompson political followers were in absolute control" (Landesco, 39).

Jim Colosimo and John Torrio were key figures in organizing prostitution in Chicago who later passed the business to Al Capone. Capone was not as favorable of vice as Colosimo and Torrio, so when he took over the position of gang leader, he focused on other aspects of organized crime such as gambling bootlegging, and labor racketeering operations.

Other markets that organized criminals were involved with before the start of Prohibition include robbery, hijacking, and contract killing. These illegal activities were not as profitable as gambling and prostitution, and were generally side products of maintaining those rackets, rather than businesses in and of themselves.

The onset of Prohibition established a setting that could be taken advantage of by organized criminals to the extent of leading to a revolution of crime to higher levels of complexity and organization (Click here for more). Additionally, "all the experience gained by years of struggle against reformers and concealed agreements with politicians was brought into service in organizing the production and distribution of beer and whiskey" (Landesco, 43). Thus, gangsters' involvement with the businesses of gambling and prostitution provided them with the skills and connections necessary to successfully exploit Prohibition, and served as a 'training ground' for such a large-scale activity.


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